KR20070026300A - 펙소페나딘 다형 및 그 제조방법 - Google Patents

펙소페나딘 다형 및 그 제조방법 Download PDF

Info

Publication number: KR20070026300A
Authority: KR; South Korea
Prior art keywords: fexofenadine; formula; crystalline fexofenadine; crystalline; free base
Prior art date: 2003-08-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

KR1020067003972A

Other languages

English (en)

Korean (ko)

Inventor

다르마라즈 라마찬드라 라오

라젠드라 나라얀라오 칸칸

마니쉬 고팔다스 간그레이드

딜리프 람다스 비라리

Original Assignee

씨아이피엘에이 엘티디.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-08-26

Filing date

2004-08-25

Publication date

2007-03-08

2004-08-25 Application filed by 씨아이피엘에이 엘티디. filed Critical 씨아이피엘에이 엘티디.

2007-03-08 Publication of KR20070026300A publication Critical patent/KR20070026300A/ko

Status Abandoned legal-status Critical Current

Links

229960003592 fexofenadine Drugs 0.000 title claims abstract description 206
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 title claims abstract description 142
238000002360 preparation method Methods 0.000 title claims description 21
150000004682 monohydrates Chemical group 0.000 claims abstract description 61
238000000034 method Methods 0.000 claims abstract description 60
239000012458 free base Substances 0.000 claims abstract description 59
RRJFVPUCXDGFJB-UHFFFAOYSA-N Fexofenadine hydrochloride Chemical group Cl.C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RRJFVPUCXDGFJB-UHFFFAOYSA-N 0.000 claims abstract description 43
230000001225 therapeutic effect Effects 0.000 claims abstract description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 72
239000000203 mixture Substances 0.000 claims description 43
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
150000001875 compounds Chemical class 0.000 claims description 37
238000006243 chemical reaction Methods 0.000 claims description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
238000002441 X-ray diffraction Methods 0.000 claims description 22
239000000739 antihistaminic agent Substances 0.000 claims description 22
229960000354 fexofenadine hydrochloride Drugs 0.000 claims description 21
239000002585 base Substances 0.000 claims description 14
239000003960 organic solvent Substances 0.000 claims description 14
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 13
238000000862 absorption spectrum Methods 0.000 claims description 13
230000001387 anti-histamine Effects 0.000 claims description 13
239000007864 aqueous solution Substances 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
-1 halo compound Chemical class 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
238000002844 melting Methods 0.000 claims description 10
230000008018 melting Effects 0.000 claims description 10
229940125715 antihistaminic agent Drugs 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 8
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
230000003301 hydrolyzing effect Effects 0.000 claims description 7
230000001376 precipitating effect Effects 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 7
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
208000024891 symptom Diseases 0.000 claims description 6
125000001246 bromo group Chemical group Br* 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000002346 iodo group Chemical group I* 0.000 claims description 5
159000000021 acetate salts Chemical class 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
239000012298 atmosphere Substances 0.000 claims description 4
238000010791 quenching Methods 0.000 claims description 4
230000000171 quenching effect Effects 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
208000009079 Bronchial Spasm Diseases 0.000 claims description 2
206010015150 Erythema Diseases 0.000 claims description 2
208000010201 Exanthema Diseases 0.000 claims description 2
206010028735 Nasal congestion Diseases 0.000 claims description 2
208000003251 Pruritus Diseases 0.000 claims description 2
208000036071 Rhinorrhea Diseases 0.000 claims description 2
206010039101 Rhinorrhoea Diseases 0.000 claims description 2
208000024780 Urticaria Diseases 0.000 claims description 2
239000013078 crystal Substances 0.000 claims description 2
201000005884 exanthem Diseases 0.000 claims description 2
150000002440 hydroxy compounds Chemical class 0.000 claims description 2
230000001035 methylating effect Effects 0.000 claims description 2
206010037844 rash Diseases 0.000 claims description 2
206010041232 sneezing Diseases 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 abstract description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 11
NLTSCOZQKALPGZ-UHFFFAOYSA-N acetic acid;dihydrate Chemical compound O.O.CC(O)=O NLTSCOZQKALPGZ-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
239000000047 product Substances 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
239000002775 capsule Substances 0.000 description 6
229960001340 histamine Drugs 0.000 description 6
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
229940079593 drug Drugs 0.000 description 5
239000012535 impurity Substances 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
206010061218 Inflammation Diseases 0.000 description 4
238000009472 formulation Methods 0.000 description 4
230000004054 inflammatory process Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
WITYUUTUSPKOAB-UHFFFAOYSA-N methyl 2-methyl-2-phenylpropanoate Chemical compound COC(=O)C(C)(C)C1=CC=CC=C1 WITYUUTUSPKOAB-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000001144 powder X-ray diffraction data Methods 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
ZVSCENGNXWPDPL-UHFFFAOYSA-N 2-methyl-2-phenylpropan-1-ol Chemical compound OCC(C)(C)C1=CC=CC=C1 ZVSCENGNXWPDPL-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
239000000428 dust Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000938 histamine H1 antagonist Substances 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
ULWORPZJUIFPIC-UHFFFAOYSA-N methyl 2-[4-(4-chlorobutanoyl)phenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)C1=CC=C(C(=O)CCCCl)C=C1 ULWORPZJUIFPIC-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
238000010979 pH adjustment Methods 0.000 description 2
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
VBTJEFSCACXENO-UHFFFAOYSA-N 2-[4-(4-chlorobutanoyl)phenyl]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=C(C(=O)CCCCl)C=C1 VBTJEFSCACXENO-UHFFFAOYSA-N 0.000 description 1
YYEROYLAYAVZNW-UHFFFAOYSA-N 2-methyl-2-phenylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=CC=C1 YYEROYLAYAVZNW-UHFFFAOYSA-N 0.000 description 1
HTDDZLNYCILZCJ-UHFFFAOYSA-N 4-chloro-1-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]butan-1-one Chemical compound OCC(C)(C)C1=CC=C(C(=O)CCCCl)C=C1 HTDDZLNYCILZCJ-UHFFFAOYSA-N 0.000 description 1
CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
241000238876 Acari Species 0.000 description 1
WTUUZDYTNKYUPI-UHFFFAOYSA-N CC(C)(C(O)=O)C1=CCCC=C1 Chemical compound CC(C)(C(O)=O)C1=CCCC=C1 WTUUZDYTNKYUPI-UHFFFAOYSA-N 0.000 description 1
OASLYWVQFXQKHC-UHFFFAOYSA-N CC(C)(C(O)=O)c1ccc(C(CCCN(CC2)CCC2C(c2ccccc2)(c2ccccc2)Cl)O)cc1 Chemical compound CC(C)(C(O)=O)c1ccc(C(CCCN(CC2)CCC2C(c2ccccc2)(c2ccccc2)Cl)O)cc1 OASLYWVQFXQKHC-UHFFFAOYSA-N 0.000 description 1
0 CC(C)(C(O*)=O)c(cc1)ccc1C(CCC*)=O Chemical compound CC(C)(C(O*)=O)c(cc1)ccc1C(CCC*)=O 0.000 description 1
XHAVWPFINLKMRN-UHFFFAOYSA-N CN(CCN)C1C=CCCC1 Chemical compound CN(CCN)C1C=CCCC1 XHAVWPFINLKMRN-UHFFFAOYSA-N 0.000 description 1
229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
208000001840 Dandruff Diseases 0.000 description 1
238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
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230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
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239000003638 chemical reducing agent Substances 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000000411 inducer Substances 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000003317 industrial substance Substances 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
150000004715 keto acids Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
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239000000825 pharmaceutical preparation Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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235000010262 sodium metabisulphite Nutrition 0.000 description 1
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238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
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235000012222 talc Nutrition 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Images

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pulmonology (AREA)
Immunology (AREA)
Ophthalmology & Optometry (AREA)
Otolaryngology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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KR1020067003972A 2003-08-26 2004-08-25 펙소페나딘 다형 및 그 제조방법 Abandoned KR20070026300A (ko)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB0319935.3		2003-08-26
GBGB0319935.3A GB0319935D0 (en)	2003-08-26	2003-08-26	Polymorphs

Publications (1)

Publication Number	Publication Date
KR20070026300A true KR20070026300A (ko)	2007-03-08

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ID=28460267

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KR1020067003972A Abandoned KR20070026300A (ko)	2003-08-26	2004-08-25	펙소페나딘 다형 및 그 제조방법

Country Status (12)

Country	Link
US (2)	US7470789B2 (fr)
EP (1)	EP1667971B1 (fr)
JP (1)	JP2007503423A (fr)
KR (1)	KR20070026300A (fr)
AU (1)	AU2004266186B2 (fr)
BR (1)	BRPI0413393A (fr)
CA (1)	CA2537257C (fr)
GB (1)	GB0319935D0 (fr)
NZ (2)	NZ545631A (fr)
RU (1)	RU2352561C2 (fr)
WO (1)	WO2005019175A1 (fr)
ZA (1)	ZA200601736B (fr)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2003248657A1 (en)	2002-06-10	2003-12-22	Teva Pharmaceutical Industries Ltd.	Polymorphic form xvi of fexofenadine hydrochloride
GB0319935D0 (en) *	2003-08-26	2003-09-24	Cipla Ltd	Polymorphs
ITMI20041143A1 (it) *	2004-06-08	2004-09-08	Dipharma Spa	Polimorfi di fexofenadina e procedimento per la loro preparazione
EP1685106A2 (fr) *	2004-09-28	2006-08-02	Teva Pharmaceutical Industries, Inc.	Forme de cristal de fexofenadine et ses processus de preparation
WO2007017905A1 (fr) *	2005-08-05	2007-02-15	Lupin Limited	Compositions pharmaceutiques de fexofenadine sous forme de suspension et destinees a une administration par voie orale
WO2007052310A2 (fr) *	2005-11-03	2007-05-10	Morepen Laboratories Limited	Polymorphes d'hydrochlorure de fexofenadine et processus de preparation de ceux-ci
ITMI20070987A1 (it) *	2007-05-16	2008-11-17	Dipharma Francis Srl	Procedimento per la preparazione di composti chetonici
WO2009034582A2 (fr) *	2007-09-13	2009-03-19	Ind-Swift Laboratories Limited	Procédé pour la préparation de chlorhydrate de fexofénadine amorphe
EP2105134A1 (fr)	2008-03-24	2009-09-30	Ranbaxy Laboratories Limited	Hydrochlorure de fexofenadine amorphe stable
WO2009136412A2 (fr) *	2008-04-25	2009-11-12	Matrix Laboratories Limited	Processus pour la préparation d’ester méthylique d’acide acétique 4-[4-(4-(hydroxydiphénylméthyl)- 1-pipéridinil]-1-oxobutyl]-α,α-diméthylbenzène et son utilisation
US8193243B2 (en)	2009-05-19	2012-06-05	Neuroderm, Ltd.	Continuous administration of dopa decarboxylase inhibitors and compositions for same
WO2011158262A1 (fr) *	2010-06-15	2011-12-22	Chemelectiva S.R.L.	Forme polymorphe du chlorhydrate de fexofénadine, intermédiaires et procédé de préparation
JP5902705B2 (ja)	2010-11-15	2016-04-13	ニューロダームリミテッドＮｅｕｒｏｄｅｒｍＬｔｄ	Ｌ−ドーパ、ドーパデカルボキシラーゼ阻害剤、カテコール−ｏ−メチルトランスフェラーゼ阻害剤、およびそれらのための組成物の継続的投与
CN102351779A (zh) *	2011-09-07	2012-02-15	浙江华纳药业有限公司	非索非那定中间体的制备方法
ITMI20120589A1 (it) *	2012-04-12	2013-10-13	Chemelectiva S R L	Intermedi utili per la sintesi di fexofenadina, processo per la loro preparazione e per la preparazione di fexofenadina
ITMI20132039A1 (it) *	2013-12-06	2015-06-07	Dipharma Francis Srl	"metodo per la preparazione di intermedi sintetici"
EP4299128A3 (fr)	2014-03-13	2024-04-17	Neuroderm Ltd.	Compositions d'inhibiteurs de dopa-décarboxylase
US10258585B2 (en)	2014-03-13	2019-04-16	Neuroderm, Ltd.	DOPA decarboxylase inhibitor compositions
CN104072402B (zh) *	2014-07-16	2016-08-17	昆山龙灯瑞迪制药有限公司	一种新结晶形式的盐酸非索非那定化合物及其制备方法
CN106380441B (zh) *	2016-08-29	2020-08-14	上海雅本化学有限公司	一种非索非那定中间体的合成方法
SI3555097T1 (sl)	2016-12-16	2022-09-30	Janssen Pharmaceutica Nv	Imidazo(4,5-d)pirolo(2,3-b)piridinske spojine kot zaviralci janus kinaz
JOP20190144A1 (ar)	2016-12-16	2019-06-16	Janssen Pharmaceutica Nv	إيميدازو بيرولو بيريدين كمثبطات لعائلة jak الخاصة بإنزيمات الكيناز
TW202016110A (zh)	2018-06-15	2020-05-01	比利時商健生藥品公司	Ｊａｋ激酶家族之小分子抑制劑
US11331293B1 (en)	2020-11-17	2022-05-17	Neuroderm, Ltd.	Method for treatment of Parkinson's disease
US11213502B1 (en)	2020-11-17	2022-01-04	Neuroderm, Ltd.	Method for treatment of parkinson's disease
US11844754B2 (en)	2020-11-17	2023-12-19	Neuroderm, Ltd.	Methods for treatment of Parkinson's disease
MX2023010642A (es)	2021-03-11	2023-11-28	Janssen Pharmaceutica Nv	Lorpucitinib para uso en el tratamiento de trastornos mediados por jak.
US12161612B2 (en)	2023-04-14	2024-12-10	Neuroderm, Ltd.	Methods and compositions for reducing symptoms of Parkinson's disease

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4254129A (en)	1979-04-10	1981-03-03	Richardson-Merrell Inc.	Piperidine derivatives
AU671822B2 (en) *	1992-04-10	1996-09-12	Aventisub Ii Inc.	4-diphenylmethyl piperidine derivatives and process for their preparation
US5654433A (en)	1993-01-26	1997-08-05	Merrell Pharmaceuticals Inc.	Process for piperidine derivatives
DK1026147T3 (da) *	1993-06-24	2004-03-22	Albany Molecular Res Inc	Forbindelser, der er anvendelige som mellemprodukter i fremstillingen af piperidinderivater
DE69527429T2 (de) *	1994-05-18	2003-03-20	Aventis Pharmaceuticals Inc., Bridgewater	Verfahren zur herstellung von wasserfreien und hydrat-formen von antihistaminischen piperinderivaten, polymerphe und pseudomorphe davon
UA64765C2 (uk) *	1997-08-14	2004-03-15	Хехст Маріон Рассел, Інк.	Спосіб підвищення біологічної доступності фексофенадину за допомогою інгібітора р-глікопротеїну, спосіб лікування та фармацевтична композиція (варіанти)
US6613906B1 (en)	2000-06-06	2003-09-02	Geneva Pharmaceuticals, Inc.	Crystal modification
CH695216A5 (de) *	2001-02-23	2006-01-31	Cilag Ag	Verfahren zur Herstellung eines nicht hydratisierten Salzes eines Piperidinderivats und eine so erhältliche neue kristalline Form eines solchen Salzes.
US20020177608A1 (en) *	2001-04-09	2002-11-28	Ben-Zion Dolitzky	Polymorphs of fexofenadine hydrochloride
BR0117054A (pt)	2001-06-18	2004-07-27	Reddys Lab Ltd Dr	Formas cristalinas do ácido 4-[4-[4-hidroxidifenilmetil)-1-piperidinil]-1-hidroxibuti l]-alfa, alfa-dimetilbenzeno acético e seu cloridrato
ES2301662T3 (es) *	2001-07-31	2008-07-01	Texcontor Etablissement	Polimorfo de clorhidrato de fexofenadina.
EP1453509A2 (fr)	2001-11-08	2004-09-08	Teva Pharmaceutical Industries Ltd.	Polymorphes a base fexofenadine
AU2003248657A1 (en)	2002-06-10	2003-12-22	Teva Pharmaceutical Industries Ltd.	Polymorphic form xvi of fexofenadine hydrochloride
GB0319935D0 (en)	2003-08-26	2003-09-24	Cipla Ltd	Polymorphs
CN1330162C (zh) *	2004-12-02	2007-08-01	华为技术有限公司	一种数据分段级联的方法

2003
- 2003-08-26 GB GBGB0319935.3A patent/GB0319935D0/en not_active Ceased
2004
- 2004-08-25 CA CA2537257A patent/CA2537257C/fr not_active Expired - Fee Related
- 2004-08-25 JP JP2006524414A patent/JP2007503423A/ja active Pending
- 2004-08-25 BR BRPI0413393-5A patent/BRPI0413393A/pt not_active IP Right Cessation
- 2004-08-25 KR KR1020067003972A patent/KR20070026300A/ko not_active Abandoned
- 2004-08-25 AU AU2004266186A patent/AU2004266186B2/en not_active Ceased
- 2004-08-25 EP EP04768180A patent/EP1667971B1/fr not_active Expired - Lifetime
- 2004-08-25 RU RU2006109480/04A patent/RU2352561C2/ru not_active IP Right Cessation
- 2004-08-25 WO PCT/GB2004/003624 patent/WO2005019175A1/fr not_active Ceased
- 2004-08-25 US US10/569,611 patent/US7470789B2/en not_active Expired - Fee Related
- 2004-08-25 NZ NZ545631A patent/NZ545631A/xx not_active IP Right Cessation
- 2004-08-25 NZ NZ580808A patent/NZ580808A/en not_active IP Right Cessation
- 2004-08-25 ZA ZA200601736A patent/ZA200601736B/en unknown
2008
- 2008-11-19 US US12/274,077 patent/US8247434B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
GB0319935D0 (en)	2003-09-24
RU2352561C2 (ru)	2009-04-20
EP1667971A1 (fr)	2006-06-14
AU2004266186A1 (en)	2005-03-03
US20070191428A1 (en)	2007-08-16
BRPI0413393A (pt)	2006-10-17
NZ580808A (en)	2011-02-25
CA2537257A1 (fr)	2005-03-03
CA2537257C (fr)	2013-07-16
US8247434B2 (en)	2012-08-21
RU2006109480A (ru)	2007-10-10
JP2007503423A (ja)	2007-02-22
NZ545631A (en)	2009-12-24
WO2005019175A1 (fr)	2005-03-03
AU2004266186B2 (en)	2009-10-22
ZA200601736B (en)	2007-05-30
US20090221830A1 (en)	2009-09-03
US7470789B2 (en)	2008-12-30
EP1667971B1 (fr)	2012-06-20

Publication	Publication Date	Title
KR20070026300A (ko)	2007-03-08	펙소페나딘 다형 및 그 제조방법
US4107310A (en)	1978-08-15	Quinoline-3-carboxamides
EP0223403B1 (fr)	1993-08-04	Dérivé de pipéridine, sa préparation et son utilisation comme médicament
EP0607536B1 (fr)	2001-01-24	Dérivés arylamidiques
JP2009040783A (ja)	2009-02-26	塩酸ドネペジルの多形結晶およびその製造法
JPH1053576A (ja)	1998-02-24	塩酸ドネペジルの多形結晶およびその製造法
KR20000064387A (ko)	2000-11-06	1-벤질-4-((5,6-디메톡시-1-인다논)-2-일)메틸피페리딘을제조하기위한방법및중간체
CA2231773A1 (fr)	1997-03-20	Derives de phenylpiperidine
US7759364B2 (en)	2010-07-20	Method for producing non-hydrated fexofenadine hydrochloride and a novel crystalline form obtained thereby
WO2008083551A1 (fr)	2008-07-17	Oxyphényl quinolines à substitution 4, composés intermédiaires, procédés d'élaboration et utilisations
KR20040012747A (ko)	2004-02-11	펙소페나딘 염산염의 다형체
JP2005350459A (ja)	2005-12-22	フェキソフェナジンの多形体およびその製造方法
AU769284B2 (en)	2004-01-22	Novel antihistaminic piperidine derivatives and intermediates for the preparation thereof
US9216955B2 (en)	2015-12-22	Polymorphic form of Fexofenadine hydrochloride, intermediates and process for its preparation
SU895291A3 (ru)	1981-12-30	Способ получени производных 4-амино-2-пиперидинохиназолина или их солей с фармацевтически приемлимыми кислотами
JPH04112868A (ja)	1992-04-14	置換ヘテロ環を有するフェニルカルボン酸誘導体
JP2967989B2 (ja)	1999-10-25	テトラヒドロピリジン誘導体及びその製法
JP2001131148A (ja)	2001-05-15	ジアステレオマ−結晶の析出方法
KR100376774B1 (ko)	2003-03-17	피페리딘 유도체 및 약학적으로 허용가능한 그것의 염의제조방법
HK1011350B (en)	2001-11-30	Arylamide derivatives
JP2005537218A (ja)	2005-12-08	フェキソフェナジン塩基の多形体
JPH0134978B2 (fr)	1989-07-21
GB2041373A (en)	1980-09-10	Quinazoline antihypertensives
JPS62181244A (ja)	1987-08-08	４〔４−（４−クロロフエニル）ブトキシ〕フエニルメチルアミン誘導体とその酸付加塩及びその製造方法
JPH02202860A (ja)	1990-08-10	安息香酸誘導体

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